Des Plaines Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by W. Ross Wells

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Des Plaines Vacation Packages

Des Plaines Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩185,932 per night from Sep 1 to Sep 2
₩185,932
₩218,257 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,956 reviews)
"We stayed in a family suite. Both rooms were large. The beds were comfortable."

Reviewed on Aug 4, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩240,154 per night from Aug 21 to Aug 22
₩240,154
₩316,539 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,827 reviews)
"Overall, staff was super friendly and helpful. Was able to check-in 2 hours early. The hotel itself is older and a little dated so the shower and toilet were working but could use an upgrade. However the room was clean and beds were comfortable. Super convenient and so many places nearby- walking ..."

Reviewed on Aug 4, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is ₩202,206 per night from Aug 24 to Aug 25
₩202,206
₩237,369 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,344 reviews)
"Great location! Clean rooms. Comfy beds."

Reviewed on Aug 5, 2025

Crowne Plaza Chicago West Loop by IHG
See all 5,056 properties in Des Plaines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Des Plaines

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Frequently asked questions

How much does a Des Plaines vacation package cost?
You'll find cheap prices on Expedia for your Des Plaines getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Des Plaines costs.
What are the cheapest months to go to Des Plaines?
You can usually find lower rates and better availability in February, September and December. Explore our cheap Des Plaines vacation packages and you could score some excellent off-season deals.
How many days is enough for Des Plaines?
The ideal duration for your Des Plaines vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the top attractions and explore some hidden spots along the way.
How to find the best Des Plaines package deals?
Finding a cheap Des Plaines package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Des Plaines package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Des Plaines vacation as a package?
You can enjoy significant savings on your next Des Plaines break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Des Plaines?
If you have your Des Plaines vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Des Plaines?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the activities available will also help you decide when to escape to Des Plaines.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Des Plaines.
  3. Decide how many days away: Start by making a list of all the activities and sights you want to get to in Des Plaines. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the right Des Plaines vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.